The Most Expensive Home in Oregon (2025 Update)

If you had unlimited resources, what would you buy? A ranch? An oceanfront beach house? An old Portland mansion? Lets see what the most expensive homes in Oregon look like.

3. 331 Metz Hill Rd, Oakland, OR

‘Heaven’s Gate Ranch’ is a 5 bed 5 bath home listed at $17,500,000, and is number three on the list of most expensive homes in Oregon. The reason it tops the price charts is the 2,670.6 acres of Umpqua Valley land that come with the home. It is currently operating as a working cattle ranch and come with plans for a 100 room hotel, restaurant, convention center, and 200-lot subdivision. While you are dreaming about future developments you can enjoy a soak in your indoor hot tub or a drink at your vintage wine bar.

2. 4311 SW Greenleaf Dr, Portland, OR

Our only Portland home making the top three, this 1930s Tudor had a recent $20 million renovation, making it the pinnacle of luxury living. Sitting atop 3.26 acres, this home serves up panoramic views of the city and mountains. You are only $25,000,000 away from owning this dream home. I guess this is about the fanciest home you could possibly get in Portland.

1. 52255 Huntington Rd, La Pine, OR

Drum roll please! Our most expensive home in Oregon is this $25,600,000 ranch in La Pine, OR, sitting on 1,499.16 acres. It checks all the boxes. Log Cabin. Private Dock. Horse Barn. Hobby Barn. Check check check check. A truly stunning piece of land for you to enjoy, if you happen to have a lot of millions of dollars.